Trickster Playing Matchmaker
by LetThemRot
Summary: Gabriel's been watching Dean and Cas stare at each other for years. He's sick of waiting around for something to happen. Destiel, with a heavy dose of Sabriel thrown in. Shurley!verse human AU.


Gabriel has been living in New York City for twenty years, and in that time he's seen a pretty full cross-section of the gay community. There have been flamers whose partners were so reserved that you'd never spot their sexuality without X-ray vision, drag queens prancing through the streets with pride flying high, drag kings with more muscle mass than the rest of the room combined. He's seen transgenders, transsexuals, every sexuality on the scale… and enough homo- and transphobia for a lifetime of nightmares. He's seen denial written as a red flag across the faces of countless men in gay bars, women glancing furtively around at strip clubs in case someone they know might be present.

He has never met someone with their head stuck as far up their ass as Dean Winchester.

It would be comical if his stupidity wasn't making Castiel miserable. As it is, though, the man is lucky; Gabriel doesn't like seeing his cousin in pain – therefore, he has given himself the right to interfere. Drastically, if necessary (Dean isn't exactly known for his romantic intellect).

He brings it up with Sam one night over pizza and beer: "Has your brother always been an idiot?"

Gabriel can't see Sam's expression from where he is sitting, tucked against the younger Winchester's side, but that surprised laughter is unmistakable. "Is this about him and Cas?"

"They're having ferociously passionate sex complete with roleplaying and fetish toys… in their imaginations. And they stare longingly at each other any time they're in the same room. Too much longer, and innocent bystanders are going to suddenly start getting pregnant, regardless of birth control or gender." He pats his pizza-filled stomach. "I'm already about three months along, myself."

"Mmhm." Sam's head lolls sideways, cheek resting against Gabriel's hair. "You certainly look it."

Gabe digs an elbow into his side. "Shut up; I'm trying to make a point. They need help, since dear Cassie's almost as bad as your brother, and they're never gonna just go have all that crazed, kinky sex of their own accord. I think we should, ya know, give 'em a little nudge to get moving."

"_We_?"

"Okay, fine, just me. You can be my backup." He feels Sam sigh underneath him. "What?"

"You've got it all plotted out already, don't you? Is this just your bizarre way of asking permission to set up my brother with your cousin? Or is it so that you're not alone with the blame when Dean finds out and tries to kill you?"

"But why _would_ he? We'll be setting him up with the man of his wet dreams. If anything, the bastard had better be on his knees thanking us when we're done. We-"

"You keep saying 'we'." Sam heaves a world-weary sigh, but his smile bleeds through into his voice. "What did you have in mind?"

Grin stretched wide, Gabriel reaches for the hand lying in Sam's lap and cradles it in both of his, tracing the knuckles with gentle fingers. He is careful to bar all traces of emotion from his voice. "I figured we'd skip the sissy stuff and just set them up on a blind date."

Another laugh startles out of Sam's chest. "You have _no_ patience… God… Dean's going to murder you."

...

It should be noted that Gabriel's plan does _not_, in fact, immediately end with him stabbed and left to die in a gutter by one flushed, outed, and embarrassed Dean Winchester. It doesn't appear to end with Dean and Cas having wild, tantric sex, either, but, well… these things take time, apparently.

Castiel joins Gabriel to get their pre-work coffee the morning after the blind date, same as always, and while he doesn't say a word about the date or its outcome, he _does_ insist on paying for both their drinks. Gabriel makes an executive decision to take that as a silent gesture of thanks. And when Dean's there the next time he swings by Castiel's apartment – fully dressed and not remotely debauched, but he's there on a Saturday afternoon, with plenty of other things that he could be doing – Gabriel carries the news home as a sure sign of victory.

Sam cracks an amused smile as he listens to him preen while they're washing dishes later that night and informs him that "you get way too much fun out of this." Tugging Gabriel into a hug, he tacks on a query: "should I be concerned for their privacy?"

"Of course not. I just want my bragging rights as soon as possible." He has to stand on his toes to reach Sam's mouth, but he manages, pleased when Sam laughs into the kiss. There are no more thoughts of Dean or Castiel for a while.

...

Progress is infuriatingly slow. A month after the initial blind date, Dean and Cas have 'gone out' once more that Gabriel knows of – when he and Sam forcibly dragged them out to a bar on a not-really-double-date.

Gabriel assigns his students an eight-page essay in frustration and is put in a foul mood five weeks later when there is almost a thousand sheets of paper stacked up on his desk to grade, and no further news from the Destiel front (Sam came up with the moniker). It's a Friday night, and grading papers is the last thing he wants to be doing, but it's no use delaying the inevitable.

Sam drops a kiss into his hair on his way out, promises to wrestle his brother and Castiel into the same room, and leaves him with the products of his exasperation. It takes a little less than ten minutes to grade one paper; he plows through twenty-two (out of one hundred and thirteen) in the next four hours.

When the door creaks open, Gabriel is still hunched over his desk, glaring at the essay in front of him, and doesn't hear it. Not until his brain registers footsteps coming into the room does he look up.

Sam is soaked through from the rain that started at some point, water dripping everywhere, teeth gleaming in the darkness of the apartment, grin stretched taunt across his face. "They danced," he offers by way of greeting. "And they sat next to each other the whole night. Neither of them seemed to have any problem with it."

"Not good enough," Gabriel mutters, turning back to the mass of wood pulp in front of his nose. A migraine is steadily building behind his eyes.

"I thought you'd be thrilled." Sam shrugs out of his jacket, then turns to rummage in the closet for a suitable hanger. "They'll catch on eventually; give it time. Cas might be your cousin, but he isn't you."

"Irrelevant," Gabriel informs an essay detailing the origin of Loki's children. "_You_came home with me that first night and just didn't leave."

"Says the man who came _swaggering_ up to me, half a dozen shots down, and made the offer in the first place." The closet door clicks shut. It takes Sam four easy strides to move into position to wrap both arms around Gabriel from behind, then pull him back until he's resting against Sam's chest, chair is balanced on two legs. "Dean's an emotional retard, and Cas isn't much better. But they'll come around, Gabe – give 'em time."

Closing his eyes, Gabriel sighs, lets himself sink into the sensation of having Sam surround him. He feels a gust of warm breath ruffle his hair. _A handful of Snickers says he's got that face-splitting grin on._ Lifting one hand, he runs it along Sam's arm until he reaches the fingers, and threads his own through them. "This's making a proper lil' matchmaker outta you, Sammy."

A hum rumbles against his back. Sam's hand curls around his, thumb stroking the long line of his wrist. "I need to get to bed," he says eventually. "Want some coffee before I go?"

Gabriel tilts his head back, staring up with wide eyes. "You're a god. Get me the peppermint?"

"Can do." Ducking down, Sam presses a kiss to his forehead, squeezes his hand a final time, then loosens his grip to tip the chair forward until it's flat on the ground again. "Be right back," he murmurs, slipping off to the kitchen.

As he listens to the coffee maker gurgle to life, Gabriel hunches over his desk again to resume staring down the paper on Loki's kids. His eyes hurt. His _brain _hurts. And there's a knot of irritation silently festering away in there. _Idiots. You don't know what you're missing. Life is so much sweeter with someone else in it._

Quiet, awkward Castiel would be more than happy to surround himself with books; he'd bask in his private shell, withdrawn, sheltered, and _alone._ Dean has cars, alcohol, porn, and friends, and most anyone who meets him could easily fall into the trap of believing that that's enough. But most people aren't living with the man's brother. Most people haven't watched him interact with Castiel – haven't personally seen his shoulders loosen, his smile widen. And most people, once upon a time, hadn't had almost the exact same philosophy. Sam had been… not _quite_ an accident, but something close. Unintentional, to say the least.

It's not that Gabriel hadn't been happy before Sam – he had been, honestly, going out to drink with old students and coworkers and friends on weekends, bringing someone home whenever the loneliness got too overbearing – but you miss out on something when you live alone. You miss out on a lot of things.

Not having to make your own coffee, for one.

Sam returns to set a steaming mug at Gabriel's elbow and a kiss atop his head, smile curling up into his eyes. "Don't stay up too late."

"Sure thing, _dear._" A metric ton of emphasis is packaged into that last word.

In response, Sam whacks his shoulder hard enough to make the chair jolt sideways. "Oops – sorry, _babe._"

"Go to bed, you mammoth." Gabriel doesn't look up, but the huffing exhale of suppressed laughter touches his ears. "Stop smirking."

A long-fingered hand drops onto his abused shoulder, squeezes briefly, then withdraws. "'Night, Gabe."

He can't help the smile that comes. "'Night, Sammy."

The apartment is conspicuously quiet after Sam vanishes into the bedroom. There's the hum of the radiator, groans from the pipes, and, far below, the weak, muffled roar of traffic from the city that never sleeps, but a warm human element is lacking. Twenty-seven months ago, on a Friday night, Gabriel would have been out drinking until he saw double, dancing until he fell down, bringing home (or going home with) anyone who would have him.

Those were fun times.

He doesn't miss them.

...

Gabriel Shurley does not give up. He hauls Dean and Castiel out for lunches and drinks and sporting events week after week, month after month – even sacrifices his precious sleep one Sunday morning in March to set up another double date for pancakes and waffles.

There is no resistance. The problem is that there's no active effort from the two parties of interest. They accept his invitations and sit next to each other and make conversation and stare at each other when they think nobody's watching… and that's it.

No kissing.

No unwarranted hugging.

No fucking in dark corners while the world slips by around them.

Just casual touches, casual words, supercharged glances… and it's all driving Gabriel insane. Even Sam is visibly irked by their romantic inertia after the breakfast date, though he keeps his mouth shut – probably to avoid giving Gabriel the satisfaction of knowing that he's not alone.

...

"Will you just fuck him already?"

It is well past midnight in Dean's apartment in SoHo – so late, in fact, that the June sun is going to make an appearance sometime in the next hour. Exams finished a few days ago, so the college students are all out en masse, clogging up bars and dance floors across the city. Sam – the youngest of the four of them – is thirty-two, and has been out of law school for six years now, but Gabriel teaches Nordic Mythology at Columbia and Castiel's one of the head librarians for the university, so they still live by that schedule.

And, after all, any possible celebration now doubles as an opportunity to get Dean and Cas together.

They'd spent last night getting far more thoroughly trashed than any respectable adults should, and when the clubs started closing, they retreated to Dean's loft in search of more alcohol. Now they're sprawled across the furniture, booze rolling sluggishly through their veins; Gabriel is happier than a pig in shit, with a grand total of zero control over what comes out of his mouth.

He's been trying to get his cousin laid for almost nine months now – long enough to complete two semesters of college, for a woman to get pregnant and give birth, and for a Nordic Mythology professor to start tearing his hair out. After watching Dean run appreciative eyes over the sprawl of Castiel's body all night, he's been feeling especially infuriated, and he's gotten progressively less reserved as his has blood-alcohol content risen.

Now, at 4:52 AM, Gabriel has finally run out of patience. He stabs an unsteady finger at the senior Winchester. "I've been watching you two for… for…fuck, _years. _Watched you watchin' each other. Fuckin' retarded, how slow you are. _Infuriatin'. _Almost enough to make a man think yer straight." He pauses, brow furrowed, to glower. "You ain't straight, are ya? I got that right?"

Dean, staring back at him with eyes bugged wide open, appears completely incapable of responding. Castiel – as ever – doesn't look much better. Both men are looking at him with expressions fit for guilty teenagers whose evangelical mother has just unearthed their stash of bestiality porn.

Beside him, Sam shifts, uneasily clearing his throat. "Gabe… not subtle. At all."

"Subtle was six months ago. Subtle was blin' dates, double dates, sendin' them to the Super Bowl t'gether. Subtle was tryin' to sit in th' background. _Fuck _subtle."

Silence punctuates the ultimatum.

Nobody moves – not even Dean, who should have beaten Gabriel half to death twenty seconds ago. That realization makes him swallow and wonder if he's just fucked up everything.

But then Castiel relaxes back against the couch, touches Dean's shoulder with a careful hand as he murmurs out "I believe that that was the sum total of the 'explosive reaction' you were expecting," and smiles.

Dean blinks three times in rapid succession and stares hard at Gabriel. "You were _serious_ about getting us together?"

_Wait, wait, wait. Abort mission. __**Abort.**_ "Ya already _were_ together?"

"Yeah! But we–I thought you were fuckin' around with the dates – a practical joke or…or…" Stuttering to a halt, Dean groans and shakes his head. "I'm too drunk for this."

Sam has been conspicuously quiet. When Gabriel glances over at him, his eyebrows are straining towards his hairline and his mouth is hanging slightly open. _Shell-shocked_ is the first word that comes to mind.

Dean gives his brother a mouth-pursed-eyes-narrowed look. "You okay, Sammy?"

"You've been together all along," Sam says weakly. It seems to be all that he's capable of vocalizing.

Clearing his throat, Castiel shakes his head. "Only for a few months." His eyes flick to Gabriel. "You came over the day after… when we first…" God help him; Cas is drunk and blushing and he's been fucking Dean Winchester for months… and Gabriel had a hand in it after all.

God help them all.

He sits up abruptly, grabbing the arm of the sofa for support, and makes a vague, frantic, waving motion at Dean with his free hand. "So I _was_ helpful, then." A round of blank stares meet the words. "I've been settin' ya _imbeciles _up on dates for _months_, and it actually… worked? I've been wastin' my time lately?"

"We are capable of independent action, ya know." The corner of Dean's mouth twitches. "But you did help. A little. Don't let it go to your head."

"Too late," Cas murmurs.

Rocking back on his seatbones, Gabriel turns a proud smirk on Sam, who rolls his eyes – but no bitchface comes into sight. He doesn't move when Gabriel kicks both legs across his and pulls himself into Sam's lap; the corners of his mouth even curl up when Gabriel grabs his chin and kisses him hard. "You're never gonna forget this, are you?" he asks, soft against Gabriel's mouth.

"Never." Gabriel kisses him again, grinning despite himself, then twists around to gaze fondly at Dean and Cas, who have now slotted comfortably together, Dean's arm across Castiel's shoulders, free hand tangled with Cas' in his lap. Gabriel beams at them. "I," he declares, "am a _fuckin' genius_."


End file.
